Think Like an Executive

with Bob Cahill

Cockpit Counsel

Think Like an Executive with Bob Cahill


As a legal professional, your work is highly visible and heavily relied on – so it’s crucial to work effectively with the executive team. On this episode of Cockpit Counsel, Bob Cahill is climbing on board. With both CEO and CFO experience, he's teaming up with Tim Parilla, CLO at LinkSquares, to share his insights.

This candid conversation will help you understand and meet expectations across the C-suite, build relationships, and much more.

Key takeaways

  • The evolution of the GC role and expectations
  • Insights on leadership and talent development
  • The importance of data-driven decision making 
  • And more! 


  • 01:47: Bob’s Career Path 
  • 03:49: Early Stage Company Experience
  • 05:23: Challenges of Leadership and Talent Development
  • 07:25: Evolution of General Counsel Role
  • 09:51: Expectations and Evolution in Legal Role
  • 10:25: Data-Driven Decision Making
  • 13:03: Centralization of Data and Business Intelligence
  • 14:30: Challenges of Transitioning to CEO
  • 19:22: Communication Tips for CLO and CEO Relationship
  • 24:35: Managing Risk and Understanding Business Objectives
  • 26:51: Embracing Technology
  • 29:12: Transitioning to Leadership Roles
  • 30:33: Developing Management and People Skills
  • 32:16: Legal's Role in Hard Conversations with the Executive Team
  • 33:07: Leading Teams in a Remote Environment
  • 35:12: Charitable Cause: Michael J Foxx Foundation


Tim Parilla Headshot
Tim ParillaChief Legal Officer, LinkSquares
Bob Cahill Former CEO and CFO